The Red Sox have a frustrating history of failing to retain homegrown stars like Jon Lester, Mookie Betts, and Anthony Rizzo. This recurring pattern has fueled fan frustration, creating the perception that the franchise is unwilling or unable to lock down its future talent. But after a tensed trade deadline that reignited memories of past missteps, the tide seems to be turning. Determined not to repeat history, the Red Sox have now sent a clear message about their intention to invest in and lock down their future stars. Proof? At just 21 years of age, rookie sensation Roman Anthony has inked an eight-year, $130 million extension with Boston, cementing his place as a cornerstone of the franchise.

It’s a monumental achievement for the young slugger, and yet, whispers are already growing. Did Anthony cash in too soon, passing up a chance at an even bigger payday down the road? One former GM of the Cincinnati Reds and Washington Nationals thinks so.

While speaking on Foul Territory, Jim Bowden, a former Reds and Nationals GM, was pretty vocal about how Anthony made the wrong call and handed the Red Sox a major bargain. “I can’t believe that Roman Anthony left that much money on the table. I am actually in a state of shock. And I don’t understand how you can sit there and watch Ronald Acuña Jr. and Vladimir Guerrero Jr. and not see the difference,” Bowden said.

Well, Ronald Acuna Jr.’s contract is often cited as one of the biggest bargains in modern-day baseball. Back in 2019, at just 21 years of age, he signed an 8-year, $100 million extension with the Braves. It was a steal for the Braves, as they locked up a generational talent well below his likely market value. “I want to continue to be a member of this organization. I want to be in this organization for the rest of my career. I’m comfortable here,” Acuna said, sharing his willingness to stay with the Braves further.

Vladimir Guerrero Jr, on the other hand, took a very different path. Earlier this year, the Blue Jays handed him a 14-year, $500 million megadeal, largely made possible because Guerrero was vocal about seeking other teams for a better paycheck. “Listen, I want to be here. I want to be a Blue Jay for the rest of my career. But it’s free agency. It’s business. So I’m going to have to listen to 29 more teams, and they’re going to have to compete for that,” he said.

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So, the messages conveyed by the two were of entirely different kinds. But what has Anthony’s approach been? Well, it’s been pretty similar to Acuna: “I knew that this is where I wanted to be, and I’m having a blast, and I just wanted to continue that,” he said.

But, Bowden feels Anthony missed the bus. While he hits free agency by the age of 29, it might be too late to fetch a record-breaking deal.

Roman Anthony has been the second hyped rookie for the Red Sox this year

Roman Anthony’s eight-year, $130 million extension is the Red Sox’s latest major investment, but not their first this season. The team previously locked in their second baseman, Kristian Campbell, with an eight-year, $60 million deal after he won the starting job in Spring Training. Notably, in his first 28 games, Campbell slashed .313/.420/.515, earning Rookie of the Month honors and quickly validating Boston’s decision to invest in him. But the shine faded just as fast.

Over the next 35 games, the 22-year-old cratered to a .154/.236/.215 line. A steep decline in production prompted the Red Sox to option him to Triple-A Worcester despite his freshly signed long-term contract. That move should serve as a warning sign for Roman Anthony. A long-term extension provides financial security and signals the organization’s faith. But it doesn’t guarantee a permanent spot in the majors. The Red Sox have already shown this year that they are willing to demote a hyped rookie if the performance falters.

So, for Anthony, staying in Boston’s lineup will depend entirely on his ability to avoid the same pitfalls that sent Campbell back to the minors!